Somewhere between year 3 and year 10, something starts to crack. The business works — on paper. But behind the scenes? You’re still holding it all together. This isn’t a failure of ambition. It’s a failure of alignment. Let’s talk about how to grow differently.

Your business “works.” On paper. But it’s starting to feel brittle. This isn’t a bandwidth issue — it’s a misalignment issue. Here’s what to do when the business you built stops feeling like the one you meant to build.

When someone on your team isn’t growing with you, the easy temptation is to blame them—or worse, to avoid the conversation altogether.

But leadership isn’t just about compassion. It’s about clarity.

If we’re serious about interrupting cycles of extraction and burnout, we need more than good intentions. We need real tools. Because misalignment doesn’t usually show up as a dramatic blowout. It creeps in slowly: missed deadlines, misunderstood priorities, mounting tension.

Not all feedback is created equal. Sometimes it's not about growth—it's about control. If you’ve ever been blindsided by a “surprise” write-up, you’re not alone. Let’s talk about why most performance management breaks trust—and what to build instead.

Big visions don’t move mountains—bulldozers do. If you’re feeling stuck between what you see and what your team can carry, it’s not a leadership flaw. It’s a systems gap. Here’s how to bridge it—with clarity, not chaos.

Most of us are still working inside the very system we want to change. So how do we start building something better—without burning it all down? In Part 5, I’m exploring the shift from burnout to regeneration. Because naming the problem isn’t enough. Let’s rebuild.

You’re told to have balance. But the system still rewards burnout. What do you do when your workplace says all the right things—but still quietly expects you to break yourself to keep things running? Here’s how to protect your capacity when the system won’t.

When leaders overcommit, they don’t create more accountability—they create more extraction. I learned this the hard way. I thought I was being a good leader—but really, I was self-exploiting. And when a leader self-exploits, the team follows their lead. Are you truly accountable… or just overcommitting?

We weren’t meant to move at this pace—but we learned to, because slowing down felt like falling behind. What happens when the speed that kept us safe is the very thing burning us out? Here’s how I’m unlearning survival mode—and what that means for the way we work.

What if the ambition that got you here… is also what’s burning you out?

For years, I felt like I was riding a fire-breathing dragon—driven by achievement, urgency, and the fear of slowing down. Then one day, the dragon landed and said: “I don’t want to breathe fire anymore.”

I didn’t know what to do with that. Because if I wasn’t constantly striving… who was I?

It turns out, I was the dragon all along. And I had the power to change the flight path.

We tell ourselves that pushing harder is the only way— that the next milestone, hire, or deal will finally bring relief. But the goalposts keep moving, and the weight of responsibility never really lifts.

And when burnout inevitably hits? The world doesn’t pause. It just asks us to self-care our way back to productivity, as if exhaustion is a personal failing rather than the result of an unsustainable system.

So, what happens when the way we work isn’t just exhausting—but unsurvivable?

Turning 40 made me take stock—not just of my accomplishments, but of my alignment. The impact I wanted to make and the systems I was operating in weren’t lining up anymore. So, I made a choice: to stop forcing what wasn’t working and start building what’s next.

Leadership is full of contradictions—power and accountability, structure and flexibility, confidence and humility. The best leaders don’t just navigate these tensions; they embrace them. But when leadership becomes reactive instead of intentional, the cost is trust, alignment, and sustainability. So, what happens when holding on too tightly is the very thing holding you back?

A mob boss and a football coach walk into your leadership strategy… what happens next? In The Sopranos and Ted Lasso, two wildly different leaders show us the extremes of fear and trust. One thrives on control, the other on belief. Watching both made me ask: What kind of leader am I? And more importantly, what kind of leader do I want to be?

The truth is, your biggest liability in business isn’t the economy or your competition—it’s you. That one thing only you can do? That’s where you’re most vulnerable. But here’s the good news: your greatest liability can become your greatest strength. Just ask Stevin John, the guy behind Blippi, who turned his business into a $20 million empire by letting go and building systems to replace himself. Let’s talk about how you can do the same.

I used to think being a 'nice' leader—someone who didn’t rock the boat—was enough. Turns out, nice doesn’t change the world. Leadership that matters requires truth-telling: owning your failures, confronting your blind spots, and creating space for real growth. The question is, are you ready to face yourself?